Friday, May 6, 2011

Is Taking a Risk Really Risky at All?

A few weeks ago, I was on the verge of crashing my first party. Techstars Demo Day had come to an end, and the NYC tech community was set to celebrate that night. (For those of you who don’t know what Techstars is, it’s an incubator in Manhattan that essentially acts as a parent and mentor for start-ups). What was amazing about this party was the fact that the guest list included anyone you’d want to meet in the tech / VC / entrepreneur community. What wasn’t so amazing was the fact that you needed a personal invite to be on this guest list- and needless to say, I didn’t have one.

Standing outside in the cold, I had a decision to make. I was faced with two options: One was to call it a night. This seemed safe. Reasonable. Easy.

The second option: Try to get in. This seemed daring. Impractical. Risky.

So I began to think- what does risky mean? What was so risky about this situation that made me so hesitant to attempt to enter the party? And if there was risk involved, what were the implications of taking such a risk and failing? As I thought about all of these questions, I began to wonder: Why am I – and people in general – so fearful of risk?

When you look in a thesaurus, three common results for “risk” are uncertainty, unpredictability, and insecurity. To me, there is an underlying context that enables all of these feelings to occur- and that is imminence.

What is imminence? To quote (from my own work), I wrote in a paper last year that:
“Imminence is about anticipation. It's that moment in time when there is complete suspense, when everything else besides the imminent ceases to exist. It can be the turning of a page of a mystery novel, the soaring of a basketball through the air just before the buzzer sounds, or the scene of a horror movie that keeps you on the edge of your seat. It's the instant when nothing's definite, nothing known fully. The imminent is unpredictable- its end result can be delightful or devastating, fulfilling or disappointing. It is this uncertainty about the imminent that causes us to be insecure- and we all fear insecurity."

So if imminence is the reason we all fear risk, how can we conquer that fear? We must conquer the imminent. And how do you conquer the imminent? You must pursue it. That’s right- to conquer the imminent you have to experience it. It might sound counterintuitive, but tell me, what’s the worst that could happen?

If you fail, what have you lost? I can tell you what you will have gained- a ton of knowledge and experience. If you believe pursuing something could be a waste of time, what do you define as a waste? To me, meeting lots of new people and trying to do something different is as fulfilling as anything else I would otherwise be doing.

Overall, my mindset is now guided by an underlying principle: I would rather do something and fail than never do it at all and always think to myself “what if.” Think about it: If you fail or make a mistake, you will undoubtedly learn and grow from it. But if you never try something at all – especially something you backed out of because of the “risks” associated with it – then there’s a chance you may be saying “what if” and regretting that decision for the rest of your life.

Now ask yourself- is THAT a risk you’re willing to take?

Is Taking a Risk Really Risky at all?


  1. I think many people are hesitant to take risks because of the whole "better safe than sorry" mentality. Now, the real question is, did you get in the party?

  2. haha I did indeed get into the party. And I am very happy to say that I am actually a TechStars Associate now! funny how things turn out...

    As for your "better safe than sorry" thought- I definitely think that causes people to be hesitant. What I'm trying to say is, people shouldn't worry about being "sorry." When it comes to taking risks, the worst thing that can happen is you fail, learn from it, and move on. And I believe that, if you fail, you'll come out as a stronger person than you were prior to taking the risk.